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Synthesis and antioxidative activity of novel acrylonitrile imidazo[4,5-b]pyridines

Imidazo[4, 5-b]pyridines, as a structural analogues of naturally occurring purines, form similar interactions with important biomacromolecules. Their derivatives posses a wide range of biological activities and some have already found application in medicine, while many others are currently in clinical testing. Imidazo-pyridines showed inhibitory activity against tumor cells and bacteria resistant to common chemotherapeutics, antioxidative activity etc. This work presents the synthesis and structural characterization of novel N-substituted acrylonitrile derived imidazo[4, 5-b]pyridines. For the synthesis of novel targeted compounds, classical organic synthesis reactions as well as microwave assisted synthesis were used. Main precursors for the synthesis of targeted derivatives were prepared by the uncatalyzed microwave assisted amination starting from corresponding halogeno-substituted precursors followed by the reduction of nitro moiety to amino. 2-cyanomethlyimidazo[4, 5-b]pyridines were obtained in the cyclocondensation reaction with ethyl cyanoacetate, while targeted acrylonitriles were prepared in condensation reaction with chosen aromatic aldehydes.1 The structures of newly prepared compounds were confirmed by means of 1H and 13C NMR spectroscopy as well as MS spectrometry. All newly prepared compounds will be tested for their antioxidative activity in vitro by using several spectroscopic (DPPH, ABTS and FRAP) as well as electrochemical methods. Additionally, the measured antioxidative capacities will be rationalized by computational analysis.2 Specifically, we will analyze the influence of the type and the number of the substituents on the imidazo[4, 5-b]pyridine scaffold in order to choose lead compound(s), which will be further optimized as promising antioxidants.

imidazo[4, 5-b]pyridines ; acrylonitriles ; antioxidative potential ; computational study

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